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Cas Database

Name	Dimethyl malonate	EINECS	203-597-8
CAS No.	108-59-8	Density	1.156 g/cm³
PSA	52.60000	LogP	-0.27750
Solubility	negligible	Melting Point	-62 °C(lit.)
Formula	C₅H₈O₄	Boiling Point	177.1 °C at 760 mmHg
Molecular Weight	132.116	Flash Point	90 °C
Transport Information	N/A	Appearance	liquid
Safety	26-36	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
Synonyms	Malonicacid, dimethyl ester (6CI,8CI);Propanedioic acid, dimethyl ester (9CI);Dimethyl 1,3-propanedioate;Dimethyl propanedioate;Methylmalonate;NSC 620046;Dimethyl Malonate (DMM);Dimethyl malonate;	Article Data	112

Dimethyl malonate Synthetic route

: 67-56-1
methanol

: 141-82-2
malonic acid

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
zirconium(IV) oxide; molybdenum at 84.85℃; for 6h; Esterification;	95%
iodine for 15h; Heating;	94%

: 141-82-2
malonic acid

: 616-38-6
carbonic acid dimethyl ester

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid at 80 - 85℃; for 2h; Neat (no solvent);	99.8%

: 16695-14-0
Malonic acid monomethyl ester

: 79-22-1
methyl chloroformate

A: 108-59-8
malonic acid dimethyl ester

B CO2: CO2

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;	A 95% B n/a

: 16695-14-0
Malonic acid monomethyl ester

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
	95%

Co2 (CO)8: Co2 (CO)8

: 96-34-4
methyl chloroacetate

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With sodium methylate In methanol	91%
With sodium hydroxide In methanol	87%

: 13750-34-0
N--p-toluolsulfonamid

A: 84274-88-4
N--p-toluolsulfonamid

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With sodium methylate; malonic acid dimethyl ester In methanol for 8h; Ambient temperature;	A 90% B 84%

: 96-34-4
methyl chloroacetate

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With potassium methanolate In methanol; Co2 (CO)8	90%

: 67-56-1
methanol

: dicobalt(η2-(C,C)-ketene)(CO)7

A: 79-20-9
acetic acid methyl ester

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With carbon monoxide In methanol Carbonylation at 50 atm.;	A 77% B 7%

: 109-84-2
2-hydroxyethylhydrazine

: dimethyl 3-(t-butylimino)-2,2-dimethylpropylidenemalonate

A: 7,7-dimethyl-2,3,7,7a-tetrahydropyrazolo<5,1-b>oxazole

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
In methanol for 8h; Heating;	A 75% B 73%

: 67-56-1
methanol

: 75-09-2
dichloromethane

: 201230-82-2
carbon monoxide

A: 109-87-5
Dimethoxymethane

B: 79-20-9
acetic acid methyl ester

C: 6290-49-9
methyl methoxyacetate

D: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; electrolysis;	A 8% B n/a C 3% D 74.5%
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; Product distribution; Mechanism; electrolysis, var. of catalyst, its reduction method, ratio;	A 8% B n/a C 3% D 74.5%
With sodium hydroxide; carbon-doped cobalt at 80℃; under 23560 Torr; for 1h;	A 1.2 % Chromat. B 7.5 % Chromat. C 1.9 % Chromat. D 28.8 % Chromat.

...Expand

Dimethyl malonate Consensus Reports

Reported in EPA TSCA Inventory.

Dimethyl malonate Specification

Dimethyl malonate, with the CAS NO.108-59-8, is a diester derivative of malonic acid. It is a common reagent for organic synthesis. It is used in the malonic ester synthesis. It is also called Dimethyl ester of malonic acid; Dimethyl propanedioate; dimethyl1,3-propanedioate; dimethylpropanedioate; MALONIC ACID,BIS-METHYL ESTER; MALONIC ACID DIMETHYL ESTER; METHYL MALONATE. Dimethyl malonate should be stored in a cool, dry place. Keep container closed when not in use.

Physical properties about Dimethyl malonate are: (1)ACD/LogP: -0.36; (2)ACD/LogD (pH 5.5): -0.36; (3)ACD/LogD (pH 7.4): -0.36; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 15.19; (7)ACD/KOC (pH 7.4): 15.18; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.402; (11)Molar Refractivity: 28.763 cm³; (12)Molar Volume: 118.034 cm³; (13)Polarizability: 11.403 10-24cm³; (14)Surface Tension: 31.9130001068115 dyne/cm; (15)Density: 1.119 g/cm³; (16)Flash Point: 90 °C; (17)Enthalpy of Vaporization: 41.338 kJ/mol; (18)Boiling Point: 177.071 °C at 760 mmHg; (19)Vapour Pressure: 1.05900001525879 mmHg at 25°C

You can still convert the following datas into molecular structure
(1)InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3;
(2)InChIKey=BEPAFCGSDWSTEL-UHFFFAOYSA-N;
(3)SmilesC(C(OC)=O)C(OC)=O;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 363, 1979.
rat	LD50	oral	5331mg/kg (5331mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 363, 1979.

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